Cheap Flights from MDW to ORL
The Cheapest Round-trip Tickets from to Orlando
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 3 December 2026 | 7 December 2026 | Direct |  | RT from 123 USD |
The Cheapest Flights for this Month from to Orlando
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 17 September 2026 | 8 November 2026 | 1 Stop | | RT from 341 USD |
| 18 September 2026 | 21 September 2026 | 1 Stop | | RT from 320 USD |
| 20 September 2026 | 8 November 2026 | Direct |  | RT from 427 USD |
| 24 September 2026 | 1 October 2026 | 1 Stop | | RT from 234 USD |
| 25 September 2026 | 28 September 2026 | 1 Stop | | RT from 236 USD |
| 3 October 2026 | 8 October 2026 | 1 Stop | | RT from 257 USD |
| 7 October 2026 | 13 October 2026 | 1 Stop | | RT from 264 USD |
| 8 October 2026 | 13 October 2026 | 1 Stop | | RT from 264 USD |
| 9 October 2026 | 12 October 2026 | 1 Stop | | RT from 317 USD |
| 2 November 2026 | 7 November 2026 | 1 Stop |  | RT from 255 USD |
| 3 November 2026 | 7 November 2026 | 1 Stop | | RT from 265 USD |
| 4 November 2026 | 8 November 2026 | 1 Stop | | RT from 320 USD |
| 5 November 2026 | 8 November 2026 | 1 Stop | | RT from 250 USD |
| 13 November 2026 | 16 November 2026 | 1 Stop | | RT from 316 USD |
| 20 November 2026 | 27 November 2026 | Direct | | RT from 150 USD |
| 21 November 2026 | 26 November 2026 | 1 Stop | | RT from 196 USD |
| 25 November 2026 | 29 November 2026 | Direct | | RT from 251 USD |
| 28 November 2026 | 9 December 2026 | 1 Stop | | RT from 321 USD |
| 3 December 2026 | 7 December 2026 | Direct | | RT from 123 USD |
| 19 December 2026 | 27 December 2026 | Direct | | RT from 364 USD |
| 29 December 2026 | 1 January 2027 | Direct | | RT from 361 USD |
| 7 January 2027 | 12 January 2027 | Direct | | RT from 324 USD |
| 20 March 2027 | 26 March 2027 | 1 Stop | | RT from 254 USD |
| 21 March 2027 | 27 March 2027 | 1 Stop | | RT from 255 USD |
The Cheapest Flights from to Orlando for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 24 September 2026 | 1 October 2026 | 1 Stop | | RT from 234 USD |
| 3 October 2026 | 8 October 2026 | 1 Stop | | RT from 257 USD |
| 20 November 2026 | 27 November 2026 | Direct | | RT from 150 USD |
| 3 December 2026 | 7 December 2026 | Direct | | RT from 123 USD |
| 7 January 2027 | 12 January 2027 | Direct | | RT from 324 USD |
| 20 March 2027 | 26 March 2027 | 1 Stop | | RT from 254 USD |